Potassium Carbonate → Methyl 2-[(2,6-dichlorobenzyl)amino]-3-(4-nitrophenyl)propanoate

HRID 1869785Notes

Reaction equation

HRID 1869785 reaction equation
[NH2:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].C([O-])([O-])=O.[K+].[K+].[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:25]=1[CH2:26]Br>CC#N>[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:25]=1[CH2:26][NH:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 560520Methyl 2-amino-3-(4-nitrophenyl)propanoate

Product 1

HCID 11269078Methyl 2-[(2,6-dichlorobenzyl)amino]-3-(4-nitrophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 2-amino-3-(4-nitrophenyl)propanoate 2 (6 g) in CH3CN (30 ml) is added, pulverized K2CO3 (11.095 g), 2,6-dichlorobenzyl bromide (6.42 g). The mixture is stirred at RT for 6 h then filtrated on decalite and evaporated. The residue is placed in CH2Cl2 (100 ml) and washed three time with water (100 ml) dried over MgSO4 and evaporated. The residue is purified by silica gel chromatography using AcOEt/hexane 10/90 as eluent.

Workup

  1. filtrationthen filtrated on decalite
  2. customevaporated
  3. washwashed three time with water (100 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-77af4de373604e2a9cb8fa413103c2c6
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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